There are a number of routes to produce higher linear alpha olefins. Traditionally lower olefins such as ethylene have been oligomerized in the presence of aluminum alkyl catalysts to yield a mixture of higher alpha olefins. The mixture must then be separated to yield different higher linear alpha olefins (LAO's). The process is not particularly selective and one can't use it to make on demand higher linear alpha olefins. Unfortunately the demand for various higher linear alpha olefins changes with time and it is difficult to shift the equilibrium to selectively produce a particular alpha olefin in a high yield.
Phillips developed a catalyst/process to selectively convert ethylene to 1-hexene. This meets a need for 1-hexene such as in the gas phase or slurry phase polymerization of ethylene hexene copolymers. However, for solution phase polymerization a significant copolymer tends to be 1-octene rather than 1-hexene.
Kuraray, Dow, Shell and Oxeno have over the last thirty years developed various homogeneous (i.e. non-supported catalyst) processes to telomerize/dimerize butadiene in the presence of a polar compound such as water, an alcohol or an acid, a stabilizing ligand and a group 9 or 10, preferably 10, metal, most preferably Pd and Pt to produce octadiene with a terminal functional group such as an alcohol, ether or ester (telomere). After the hydrogenation of the double bonds the functional group may be removed from the telomere typically in the presence of an acid catalyst (e.g. alumina) resulting in the formation of 1-octene. Representative of these types of processes are U.S. Pat. No. 4,417,079 issued Nov. 22, 1983 to Yoshimura et al., assigned to Kuraray Company Limited; U.S. Pat. No. 5,030,792 issued Jul. 9, 1991 to Slaugh, assigned to Shell Oil Company; and WO 92/10450 published Jun. 25, 1992 in the name of Bohley et al., assigned to Dow Benelux N. V. This art uses an unsupported catalyst which is soluble in the reaction medium (homogeneous catalyst). Metals such as Rh, Pd, and Pt are extremely expensive and any loss of the catalyst has a strong negative impact on the economics of the process.
The present invention seeks to provide a process for the telomerization of alkadienes to octadiene substituted in position 1 with a functional group containing an oxygen atom (typically an alcohol or ether) in the presence of a stable heterogeneous (i.e. supported) catalyst from which there is only a very low loss of metal.